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ipod classic 160gb problems loading music

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Hello all, Ive been trying to add music to this Ipod for 3 days now. The problem is as follow.
When I first plug it in it gives me a message that It is unrecognized and have to restore it. When I do restore it goes back to the same message asking to restore. After a while it passes that step and lets me add music.

when I attempt to sync it with 1000 songs it never finishes and gives me this error below

attempting to copy to the disc "ipod" Failed.an unknown error occurred (-69).

Once it gives me this error I eject the ipod and the Ipod is empty with no music.
I have tried everything and cannot get this think to load music. Any help would be greatly appreciated.
I have the latest Itunes and classic ipod software

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